The present invention relates to novel N-substituted (2R,3S,4S,5R,6R,10R,11R)-3-[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-r ibohexopyranosyl)-oxy]-5-[(3,4,6-trideoxy-3-amino-.beta.-D-xylohexopyranosy l)-oxy]-2,4,6,8,10-pentamethyl-11-acetyl-12,13-dioxabicyclo[8.2.1]-tridec-8 -en-1-one compounds with motilin-agonistic properties and to the acid addition salts thereof and also to pharmaceutical formulations containing these compounds and to processes for the preparation of these compounds. The compounds according to the invention are ring-contracted N-demethyl-N-isopropyl derivatives of erythromycin A with a modified side chain.
The antibiotic erythromycin A is known to have, in addition to its antibiotic effects, also gastrointestinal side effects which are undesirable for antibiotics, inter alia a great increase in the contraction activity in the gastrointestinal region with gastric and intestinal cramps, nausea, vomiting and diarrhoea.
There have been several attempts to modify erythromycin A so as to obtain derivatives in which the antibiotic effect is virtually no longer present, but an effect influencing the motility of the gastrointestinal tract is retained. U.S. Pat. No. 5,418,224 (=EP 550,895) discloses ring-contracted N-demethyl-N-isopropyl-erythromycin A derivatives having gastrointestinally effective motilin-agonistic properties.
Furthermore, similar ring-contracted erythromycin derivatives are known from U.S. Pat. No. 5,106,961 (=EP 382,472), but these have antibiotic effects.